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18 Headmaster Tubes Elephant Tube List

Some girls need the stiff hand of a man to best learn their lesson, and thats what was needed for Lina. She had repeatedly disrespected her headmaster, and so it was time for him to ensure it would never happen again. He ensured her ass was as red as hi

Some girls need the stiff..

The headmaster sometimes doubles as the doctor of the school, were he performs humanitarian efforts. Despite the sometimes unfortunate times, he still has to perform his duties as punisher of the school. Arianie had been found in a risque outfit, posing

The headmaster sometimes..

Nikki is at it again, this time with a problem in gym leading to her latest punishment. The headmaster picked up a wooden staff, knowing the full effect it would have on her. He repeatedly struck her until bruises began to appear, reminders for the rest

Nikki is at it again, thi..

Lucie has disobeyed her teacher one too many times and is called into the headmasters office for a good caning. With help from another teacher, the headmaster bends Lucie over a desk and binds her arms and legs. He lowers her panties, lifts her skirt an

Lucie has disobeyed her t..

Sexy little Lexi is sent away by her headmaster for a transatlantic education she won't forget. Across the pond she encounters likeminded bad girls who happily lead her astray. Before she knows it she's receiving a hardcore lesson in sucking and fucking. George Uhl Jazz Duro Mackenzee Pierce

Sexy little lexi is sent..

Angela was a good student, always wanting everyone to like her. This came to a head though when she was basically forced to go out with a few girls from the school. The night involved drinking and partying. Once the headmaster found out about this, he

Angela was a good student..

$Nikki was back in class, and had -forgotten- to go to class the day before. The headmaster remembered her past infractures, and felt that she was headed towards a downward slope. This is when she was taken to the -individual- instruction room. She knew$

Nikki was back in class,..

The headmaster has just caught Katja trying to sneak out after curfew and drags her into his office to teach her a lesson. He pulls her over his lap, lifts up her skirt and gives her an ATK spanking. He then orders her to pull down her panties so he can

The headmaster has just c..

Shannon knows what happens when she stays out to late, but does it anyway and is called into the headmasters office to receive her punishment. The headmaster orders Shannon to remove her dress, places her in a guillotine and uses his cane to turn he bott

Shannon knows what happen..

Sexy little Lexi is sent away by her headmaster for a transatlantic education she won't forget. Across the pond she encounters likeminded bad girls who happily lead her astray. Before she knows it she's receiving a hardcore lesson in sucking and fucking. George Uhl Jazz Duro Mackenzee Pierce

Sexy little lexi is sent..

Charlie has disobeyed her teacher yet again and is called into the headmasters office to be disciplined. The headmaster pulls her across his lap, lifts up her skirt and proceeds to give her a good old-fashioned spanking. After a few swats of his hand, t

Charlie has disobeyed her..

Shelia is a girly maid who loves to wear a pink apron while she cleans the headmasters house. The headmaster has told Shelia he hates the color pink and decides to punish her for disobeying him. He grabs her by the arm, throws her over his knee and proce

Shelia is a girly maid wh..

Josephine is a perfect example of a bad girl gone worse. She had been paddled spanked, paddled, and caned, but for some reason her attitude and behavior never seemed to change. This is when the headmaster had enough, and now felt it was time to place her

Josephine is a perfect ex..

Eva had been walking around school without panties flashing her fellow classmates. She saw this as a big joke, and a way to make her dull life all the more exciting. The headmaster however saw this and took immediate action. She was not to make a mocke

Eva had been walking arou..

The headmaster and the teacher place Tina in a guillotine then lift up her dress and give her a lashing she wont soon forget

The headmaster and the te..

Kristy has failed to properly clean the windows and must be punished. The headmaster throws her over his knee and gives her a good old-fashioned ATK spanking. After a few swats with his hand, he orders her to remove her panties and continues the spankin

Kristy has failed to prop..

The spanking in this video is a testament to how vicious the headmaster can be to certain students. Sandra hadnt really done anything wrong as of late but it was felt she would eventually do something, as she had been more and more bold about her demeano

The spanking in this vide..

Katty has recently dyed her hair, something the school forbids. The headmaster gets word of this, calls Katty to his office and pulls her over his lap to administer her punishment. He lifts up her skirt, lowers her panties and gives her an OTK spanking

Katty has recently dyed h..

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